The present invention describes novel compositions of matter consisting of molecules containing an amine oxide and phosphate ester as part of the same compound. Although, amine oxide and phosphate ester containing molecules as distinct compounds are known in the prior art, the combination of these two functional groups on the same molecule has not been disclosed or suggested. The literature describing the preparation of fatty alkyl based amine oxides and phosphate esters is both extensive and well known to those of ordinary skill in the art of surfactant manufacture and use; therefore it need not be reviewed. References to fatty alkyl based molecules with tertiary amine oxide and the salts of covalently bound acid groups on the same molecule are much less evident. For example Engelmann (U.S. Pat. No. 2,159,967) teaches the preparation and use of tertiary amine oxide carboxylates and sulfonates separated by 1 to 4 carbon atoms. Ulrich (U.S. Pat. No. 2,185,163) describes a rather ill defined tertiary amine oxide polyethoxylate subsequently sulphonated. Cahn and Kaniecki (U.S. Pat. No. 3,267,135 and 3,359,208 amongst others) teach the preparation and use of N-(2-hydroxyalkyl-)N-Methyltaurine-N-oxides. Stanford and Vogelsang (U.S. Pat. Nos. 3,477,956; 3,692,881; 3,728,419 and 3,787,534,) teach the preparation and use of phosphated hydroxy amines but do not mention or suggest conversion of the subsequent tertiary amine phosphate ester salt into an amine oxide derivative.
Tertiary amine oxides when acidified to low pH exist as cationic materials with three alkyl and one hydroxyl substituents; therefore, they can be considered under these conditions as quaternary ammonium derivatives. Surfactant molecules containing both quaternary ammonium and phosphate esters on the same molecule are known. For example, Verdicchio (U.S. Pat. No. 4,132,657) teaches the preparation of complex phosphate ester surfactants derived from a quaternary dihydroxy compound. Mayhew (U.S. Pat. No. 4,209,449) describes phosphate quaternaries prepared by the interaction of the tiglycidyl ester of mono sodium phosphate and selected tertiary aminoamides. Similiar chemistry is disclosed by Lindemann et. al. (U.S. Pat. No. 4,215,064) dealing with selected mono and di glycidyl phosphate ester quaternizing agents and their reaction with a variety of selected fatty tertiary amines. Similiar reactions were originally described however by Shen (U.S. Pat. No. 3,304,349) who teaches the preparation in general of acid containing glycidyl ethers and their reaction into tertiary amines to form amphoteric or Zwitterionic fatty based surfactants.
Phosphorus may be in other oxidation states. For example Diery (U.S. Pat. No. 3,856,893) is the first of a series (U.S. Pat. No. 3,888,978; 3,922,344 and 3,928,509) teaches the reaction of 1,3-dioxa-2-phosphorinanes with various tertiary amines to form hybrid ionic phosphorus compounds containing phosphate and quaternary ammonium salts attached to the same molecule.
Organo-phosphono-amine oxide compounds are disclosed by Crutchfield and Irani (U.S. Pat. No. 3,429,914 and 3,483,178). They are prepared from amines, aldehydes and phosphorus acid. The condensation product of this reaction is then converted to an amine oxide with for example hydrogen peroxide.
The phosphated amine oxide compounds of the present invention exhibit outstanding foaming, wetting, cleansing, viscosity-building, emulsification, lubricity and antistatic properties; therefore, they are of excellent utility in many industrial applications requiring surface active agents. Unlike the amine oxides, the phosphated derivatives resist loss by volatility from hot surfaces. This property allows these novel compounds to function as fiber processing aids where the processes call for high temperature exposure. In addition the greatly reduced volatility eliminates the change of atmospheric pollution.
The multiplicity of ionic charge of these compounds also allows them to function as surfactants in the presence of strong electrolytes such as sodium hydroxide. This affords foam generation in the presence of strong electrolytes which is a desireable aid in cleaning. Foam stabilization is also achieved with selected candidates.